Chinese Journal of Organic Chemistry >
Advances in the Synthesis of Carboxylic Acid by Photochemical Conversion of CO2
Received date: 2024-05-06
Revised date: 2024-07-04
Online published: 2024-07-25
Supported by
National Natural Science Foundation of China(22271293); Young Scientists in Basic Research of Chinese Academy of Sciences(YSBR-050)
The pursuit of cleanliness, energy efficiency, and resource preservation through photochemical reactions has led to the emergence of novel pathways and methodologies in synthetic chemistry, rendering it one of the most dynamic research domains within modern organic synthesis. Carbon dioxide (CO2), owing to its non-toxic, cost-effective, abundant, and recyclable attributes, serves as an optimal C1 precursor in synthetic chemistry. Recent years have witnessed rapid advancements in the photochemical conversion of CO2 into carboxylic acid compounds, offering a gentle and highly efficient synthetic approach for their production. An overview of the research progress on the synthesis methodologies of carboxylic acid compounds through photochemical CO2 conversion is provided, while certain associated reaction mechanisms are also elucidated.
Key words： carbon dioxide; photocatalysis; carboxylation
Panfeng Yuan , Canming Zhu , Qingyuan Meng . Advances in the Synthesis of Carboxylic Acid by Photochemical Conversion of CO2[J]. Chinese Journal of Organic Chemistry, 2024 , 44(10) : 2997 -3042 . DOI: 10.6023/cjoc202405004
| [1] | (a) Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102. |
| [1] | (b) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. |
| [1] | (c) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075. |
| [1] | (d) Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. J. Org. Chem 2016, 81, 6898. |
| [1] | (e) Skubi, K. L.; Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, 116, 10035. |
| [2] | Ye, J.-H.; Ju, T.; Huang, H.; Liao, L.-L.; Yu, D.-G. Acc. Chem. Res. 2021, 54, 2518. |
| [3] | Yeung, C. S. Angew. Chem., Int. Ed. 2019, 58, 5492. |
| [4] | Jung, J.; Saito, S. Synthesis 2021, 53, 3263. |
| [5] | (a) Fan, Z.; Zhang, Z.; Xi, C. ChemSusChem 2020, 13, 6201. |
| [5] | (b) He, X.; Qiu, L.-Q.; Wang, W.-J.; Chen, K.-H.; He, L.-N. Green Chem. 2020, 22, 7301. |
| [5] | (c) Pradhan, S.; Roy, S.; Sahoo, B.; Chatterjee, I. Chem.-Eur. J. 2021, 27, 2254. |
| [5] | (d) Zhang, G.; Cheng, Y.; Beller, M.; Chen, F. Adv. Synth. Catal. 2021, 363, 1583. |
| [5] | (e) Dou, Q.; Wang, T.; Li, S.; Fang, L.; Zhai, H.; Cheng, B. Chin. J. Org. Chem. 2022, 42, 4257. (in Chinese) |
| [5] | (窦谦, 汪太民, 李嗣锋, 房丽晶, 翟宏斌, 程斌, 有机化学, 2022, 42, 4257.) |
| [6] | Shimomaki, K.; Murata, K.; Martin, R.; Iwasawa, N. J. Am. Chem. Soc. 2017, 139, 9467. |
| [7] | Meng, Q.-Y.; Wang, S.; K?nig, B. Angew. Chem., Int. Ed. 2017, 56, 13426. |
| [8] | Hang, W.; Li, D.; Zou, S.; Xi, C. J. Org. Chem 2023, 88, 5007. |
| [9] | Zhu, C.; Zhang, Y.-F.; Liu, Z.-Y.; Zhou, L.; Liu, H.; Feng, C. Chem. Sci. 2019, 10, 6721. |
| [10] | Yan, S.-S.; Liu, S.-H.; Chen, L.; Bo, Z.-Y.; Jing, K.; Gao, T.-Y.; Yu, B.; Lan, Y.; Luo, S.-P.; Yu, D.-G. Chem 2021, 7, 3099. |
| [11] | Bo, Z.-Y.; Yan, S.-S.; Gao, T.-Y.; Song, L.; Ran, C.-K.; He, Y.; Zhang, W.; Cao, G.-M.; Yu, D.-G. Chin. J. Catal. 2022, 43, 2388. |
| [12] | Liao, L.-L.; Cao, G.-M.; Ye, J.-H.; Sun, G.-Q.; Zhou, W.-J.; Gui, Y.-Y.; Yan, S.-S.; Shen, G.; Yu, D.-G. J. Am. Chem. Soc. 2018, 140, 17338. |
| [13] | Chen, L.; Qu, Q.; Ran, C.-K.; Wang, W.; Zhang, W.; He, Y.; Liao, L.-L.; Ye, J.-H.; Yu, D.-G. Angew. Chem., Int. Ed. 2023, 62, e202217918. |
| [14] | Shimomaki, K.; Nakajima, T.; Caner, J.; Toriumi, N.; Iwasawa, N. Org. Lett. 2019, 21, 4486. |
| [15] | Cao, K.; Fan, D.; Gao, M.; Fan, B.; Chen, N.; Wang, L.; Tian, P.; Liu, Z. ACS Catal. 2022, 12, 1. |
| [16] | Fan, Z.; Chen, S.; Zou, S.; Xi, C. ACS Catal. 2022, 12, 2781. |
| [17] | Li, W.-D.; Wu, Y.; Li, S.-J.; Jiang, Y.-Q.; Li, Y.-L.; Lan, Y.; Xia, J.-B. J. Am. Chem. Soc. 2022, 144, 8551. |
| [18] | Gao, T.-Y.; Mo, X.-Y.; Zhang, S.-R.; Jiang, Y.-X.; Luo, S.-P.; Ye, J.-H.; Yu, D.-G. Chin. Chem. Lett. 2024, 35, 109364. |
| [19] | Fan, Z.; Yi, Y.; Chen, S.; Xi, C. Org. Lett. 2021, 23, 2303. |
| [20] | (a) Wheland, R.; Bartlett, P. D. J. Am. Chem. Soc. 1970, 92, 6057. |
| [20] | (b) Sander, W. W. J. Org. Chem 1989, 54, 4265. |
| [21] | Masuda, Y.; Ishida, N.; Murakami, M. J. Am. Chem. Soc. 2015, 137, 14063. |
| [22] | Ishida, N.; Masuda, Y.; Uemoto, S.; Murakami, M. Chem.-Eur. J. 2016, 22, 6524. |
| [23] | Seo, H.; Katcher, M. H.; Jamison, T. F. Nat. Chem. 2017, 9, 453. |
| [24] | Meng, Q.-Y.; Schirmer, T. E.; Berger, A. L.; Donabauer, K.; K?nig, B. J. Am. Chem. Soc. 2019, 141, 11393. |
| [25] | Ishida, N.; Masuda, Y.; Imamura, Y.; Yamazaki, K.; Murakami, M. J. Am. Chem. Soc. 2019, 141, 19611. |
| [26] | Sahoo, B.; Bellotti, P.; Juliá-Hernández, F.; Meng, Q.-Y.; Crespi, S.; K?nig, B.; Martin, R. Chem.-Eur. J. 2019, 25, 9001. |
| [27] | Song, L.; Fu, D.-M.; Chen, L.; Jiang, Y.-X.; Ye, J.-H.; Zhu, L.; Lan, Y.; Fu, Q.; Yu, D.-G. Angew. Chem., Int. Ed. 2020, 59, 21121. |
| [28] | Schmalzbauer, M.; Svejstrup, T. D.; Fricke, F.; Brandt, P.; Johansson, M. J.; Bergonzini, G.; K?nig, B. Chem 2020, 6, 2658. |
| [29] | Jiang, Y.-X.; Liao, L.-L.; Gao, T.-Y.; Xu, W.-H.; Zhang, W.; Song, L.; Sun, G.-Q.; Ye, J.-H.; Lan, Y.; Yu, D.-G. Nat. Synth. 2024, 3, 394. |
| [30] | Lapidus, A. L.; Pirozhkov, S. D.; Koryakin, A. A. Russ. Chem. Bull. 1978, 27, 2513. |
| [31] | Williams, C. M.; Johnson, J. B.; Rovis, T. J. Am. Chem. Soc. 2008, 130, 14936. |
| [32] | Greenhalgh, M. D.; Thomas, S. P. J. Am. Chem. Soc. 2012, 134, 11900. |
| [33] | (a) Ostapowicz, T. G.; Schmitz, M.; Krystof, M.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2013, 52, 12119. |
| [33] | (b) Kawashima, S.; Aikawa, K.; Mikami, K. Eur. J. Org. Chem. 2016, 2016, 3166. |
| [34] | Shao, P.; Wang, S.; Chen, C.; Xi, C. Org. Lett. 2016, 18, 2050. |
| [35] | Wu, L.; Liu, Q.; Fleischer, I.; Jackstell, R.; Beller, M. Nat. Commun. 2014, 5, 3091. |
| [36] | Murata, K.; Numasawa, N.; Shimomaki, K.; Takaya, J.; Iwasawa, N. Chem. Commun. 2017, 53, 3098. |
| [37] | Seo, H.; Liu, A.; Jamison, T. F. J. Am. Chem. Soc. 2017, 139, 13969. |
| [38] | Meng, Q.-Y.; Wang, S.; Huff, G. S.; K?nig, B. J. Am. Chem. Soc. 2018, 140, 3198. |
| [39] | Saini, S.; Singh, H.; Prajapati, P. K.; Sinha, A. K.; Jain, S. L. ACS Sustainable Chem. Eng. 2019, 7, 11313. |
| [40] | Huang, H.; Ye, J.-H.; Zhu, L.; Ran, C.-K.; Miao, M.; Wang, W.; Chen, H.; Zhou, W.-J.; Lan, Y.; Yu, B.; Yu, D.-G. CCS Chem. 2021, 3, 1746. |
| [41] | Song, L.; Wang, W.; Yue, J.-P.; Jiang, Y.-X.; Wei, M.-K.; Zhang, H.-P.; Yan, S.-S.; Liao, L.-L.; Yu, D.-G. Nat. Catal. 2022, 5, 832. |
| [42] | Yatham, V. R.; Shen, Y.; Martin, R. Angew. Chem., Int. Ed. 2017, 56, 10915. |
| [43] | Ye, J.-H.; Miao, M.; Huang, H.; Yan, S.-S.; Yin, Z.-B.; Zhou, W.-J.; Yu, D.-G. Angew. Chem., Int. Ed. 2017, 56, 15416. |
| [44] | Hou, J.; Ee, A.; Cao, H.; Ong, H.-W.; Xu, J.-H.; Wu, J. Angew. Chem., Int. Ed. 2018, 57, 17220. |
| [45] | Fu, Q.; Bo, Z.-Y.; Ye, J.-H.; Ju, T.; Huang, H.; Liao, L.-L.; Yu, D.-G. Nat. Commun. 2019, 10, 3592. |
| [46] | Mello, R.; Arango-Daza, J. C.; Varea, T.; González-Nú?ez, M. E. J. Org. Chem 2018, 83, 13381. |
| [47] | Zhang, B.; Yi, Y.; Wu, Z.-Q.; Chen, C.; Xi, C. Green Chem. 2020, 22, 5961. |
| [48] | Hahm, H.; Kim, J.; Ryoo, J. Y.; Han, M. S.; Hong, S. Org. Biomol. Chem. 2021, 19, 6301. |
| [49] | Niu, Y.-N.; Jin, X.-H.; Liao, L.-L.; Huang, H.; Yu, B.; Yu, Y.-M.; Yu, D.-G. Sci. China: Chem. 2021, 64, 1164. |
| [50] | Wang, H.; Gao, Y.; Zhou, C.; Li, G. J. Am. Chem. Soc. 2020, 142, 8122. |
| [51] | Liao, L.-L.; Cao, G.-M.; Jiang, Y.-X.; Jin, X.-H.; Hu, X.-L.; Chruma, J. J.; Sun, G.-Q.; Gui, Y.-Y.; Yu, D.-G. J. Am. Chem. Soc. 2021, 143, 2812. |
| [52] | Zhou, C.; Li, M.; Sun, J.; Cheng, J.; Sun, S. Org. Lett. 2021, 23, 2895. |
| [53] | Yang, H.; Yao, Y.; Yang, Q.; Yao, Y.; Sun, J.; Sun, S. Org. Lett. 2024, 26, 4194. |
| [54] | Benedetti Vega, K.; Campos Delgado, J. A.; Pugnal, L. V. B. L.; K?nig, B.; Menezes Correia, J. T.; Weber Paix?o, M. Chem.-Eur. J. 2023, 29, e202203625. |
| [55] | Zhang, W.; Chen, Z.; Jiang, Y.-X.; Liao, L.-L.; Wang, W.; Ye, J.-H.; Yu, D.-G. Nat. Commun. 2023, 14, 3529. |
| [56] | Yue, J.-P.; Xu, J.-C.; Luo, H.-T.; Chen, X.-W.; Song, H.-X.; Deng, Y.; Yuan, L.; Ye, J.-H.; Yu, D.-G. Nat. Catal. 2023, 6, 959. |
| [57] | Zhang, B.; Li, T.-T.; Mao, Z.-C.; Jiang, M.; Zhang, Z.; Zhao, K.; Qu, W.-Y.; Xiao, W.-J.; Chen, J.-R. J. Am. Chem. Soc. 2024, 146, 1410. |
| [58] | Ju, T.; Zhou, Y.-Q.; Cao, K.-G.; Fu, Q.; Ye, J.-H.; Sun, G.-Q.; Liu, X.-F.; Chen, L.; Liao, L.-L.; Yu, D.-G. Nat. Catal. 2021, 4, 304. |
| [59] | Yu, B.; Liu, Y.; Xiao, H.-Z.; Zhang, S.-R.; Ran, C.-K.; Song, L.; Jiang, Y.-X.; Li, C.-F.; Ye, J.-H.; Yu, D.-G. Chem 2024, 10, 938. |
| [60] | Xu, P.; Wang, S.; Xu, H.; Liu, Y.-Q.; Li, R.-B.; Liu, W.-W.; Wang, X.-Y.; Zou, M.-L.; Zhou, Y.; Guo, D.; Zhu, X. ACS Catal. 2023, 13, 2149. |
| [61] | Zhang, F.; Wu, X.-Y.; Gao, P.-P.; Zhang, H.; Li, Z.; Ai, S.; Li, G. Chem. Sci. 2024, 15, 6178. |
| [62] | Hou, J.; Ee, A.; Feng, W.; Xu, J.-H.; Zhao, Y.; Wu, J. J. Am. Chem. Soc. 2018, 140, 5257. |
| [63] | Zhou, W.-J.; Wang, Z.-H.; Liao, L.-L.; Jiang, Y.-X.; Cao, K.-G.; Ju, T.; Li, Y.; Cao, G.-M.; Yu, D.-G. Nat. Commun. 2020, 11, 3263. |
| [64] | Gao, Y.; Wang, H.; Chi, Z.; Yang, L.; Zhou, C.; Li, G. CCS Chem. 2022, 4, 1565. |
| [65] | Yi, Y.; Xi, C. Chin. J. Catal. 2022, 43, 1652. |
| [66] | Yi, Y.; Fan, Z.; Xi, C. Green Chem. 2022, 24, 7894. |
| [67] | Gao, W.; Yang, Q.; Yang, H.; Yao, Y.; Bai, J.; Sun, J.; Sun, S. Org. Lett. 2024, 26, 467. |
| [68] | Ju, T.; Fu, Q.; Ye, J.-H.; Zhang, Z.; Liao, L.-L.; Yan, S.-S.; Tian, X.-Y.; Luo, S.-P.; Li, J.; Yu, D.-G. Angew. Chem., Int. Ed. 2018, 57, 13897. |
| [69] | Fan, X.; Gong, X.; Ma, M.; Wang, R.; Walsh, P. J. Nat. Commun. 2018, 9, 4936. |
| [70] | Cao, G.-M.; Hu, X.-L.; Liao, L.-L.; Yan, S.-S.; Song, L.; Chruma, J. J.; Gong, L.; Yu, D.-G. Nat. Commun. 2021, 12, 3306. |
| [71] | Okumura, S.; Uozumi, Y. Org. Lett. 2021, 23, 7194. |
| [72] | (a) Giezendanner, H.; M?rky, M.; Jackson, B.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1972, 55, 745. |
| [72] | (b) Padwa, A.; Wetmore, S. I., Jr. J. Am. Chem. Soc. 1974, 96, 2414. |
| [73] | Jiang, Y.-X.; Chen, L.; Ran, C.-K.; Song, L.; Zhang, W.; Liao, L.-L.; Yu, D.-G. ChemSusChem 2020, 13, 6312. |
| [74] | Xiao, H.-Z.; Yu, B.; Yan, S.-S.; Zhang, W.; Li, X.-X.; Bao, Y.; Luo, S.-P.; Ye, J.-H.; Yu, D.-G. Chin. J. Catal. 2023, 50, 222. |
| [75] | Yuan, P.-F.; Yang, Z.; Zhang, S.-S.; Zhu, C.-M.; Yang, X.-L.; Meng, Q.-Y. Angew. Chem., Int. Ed. 2024, 63, e202313030. |
| [76] | Yuan, P.-F.; Meng, Q.-Y. Synlett 2024, 35, A-J. |
| [77] | Cao, K.-G.; Gao, T.-Y.; Liao, L.-L.; Ran, C.-K.; Jiang, Y.-X.; Zhang, W.; Zhou, Q.; Ye, J.-H.; Lan, Y.; Yu, D.-G. Chin. J. Catal. 2024, 56, 74. |
| [78] | Duan, D.; Ma, Y.; Liu, Y.; Cheng, F.; Zhu, D.; Wang, S. Chin. J. Org. Chem. 2024, 44, 1675. (in Chinese) |
| [78] | (段东森, 马媛, 刘宇博, 程富, 朱道勇, 王少华, 有机化学, 2024, 44, 1675.) |
/
| 〈 |
|
〉 |
